CN102085223A - Sweet osmanthus flower extractive as well as preparation method and application thereof to liver protection - Google Patents
Sweet osmanthus flower extractive as well as preparation method and application thereof to liver protection Download PDFInfo
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- CN102085223A CN102085223A CN2009102731000A CN200910273100A CN102085223A CN 102085223 A CN102085223 A CN 102085223A CN 2009102731000 A CN2009102731000 A CN 2009102731000A CN 200910273100 A CN200910273100 A CN 200910273100A CN 102085223 A CN102085223 A CN 102085223A
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Abstract
The invention provides a sweet osmanthus flower extractive, which has an effect of protecting the liver and is prepared by taking sweet osmanthus flowers as a raw material through the steps of extracting with an organic solvent, decompressing and concentrating an extracting solution and refining with a macroporous resin. Animal experiments show that the substance has an obvious effect of protecting the liver. In the invention, sweet osmanthus flowers are comprehensively utilized, the adopted technical route is simple, convenient and feasible and has little pollution to the environment, and the purity of the prepared effective substance can reach above 90%.
Description
Technical field
The present invention relates to a kind of Flos Osmanthi Fragrantis hepatoprotective active substance and its production and application, be specifically related to from Flos Osmanthi Fragrantis, extract the preparation method and the application of hepatoprotective active substance.
Technical background
China is the multiple state of hepatopathy, and the hepatopath accounts for 12～15% of total population, and wherein about 10% hepatopath can develop into hepatocarcinoma and liver cirrhosis, and the hepatopathy M ﹠ M is only second to cardiovascular diseases and cancer and occupies the 3rd.The hepatopathy pathogenic factor has: viral infection, drug induced injury, ethanol or chemical stimulation etc., they all show as in various degree hepatocyte injury in the hepatopathy active stage.The treatment of antagonism hepatopathy mainly comprises two aspects: the one, at the etiological treatment of protopathy; The 2nd, to the treatment of hepatocyte injury itself, mainly implement hepatoprotective clinically by medicine.Therefore, searching effectively protects the liver the focus that material is medicine and pharmacology worker concern always.Plant amedica has the characteristics of too many levels, multi-level, many target spots comprehensive function, aspect the treatment hepatopathy special advantages is being arranged.For example, silymarin (silymarin) is a kind of natural flavone lignanoid mixture of separation and purification from the Herba Silybi mariani fruit, its main mechanism is repaired and regeneration for removing free radical, lipoid peroxidization resistant and promotion hepatocyte, makes it become the clinical natural liver protection active drug that is used for of generally acknowledging in the world at present.
Flos Osmanthi Fragrantis (Osmanthus fragrans Lour.), chain timbers Rhinocerotidae evergreen shrubs or dungarunga, Flos Osmanthi Fragrantis is at the cultivation history in existing 2500 of China.Flos Osmanthi Fragrantis except that for view and admire, the cuisines, root, flower and fruit be all pharmaceutically acceptable to be removed sickly, warm in nature, acrid in the mouth, nontoxic has the function of reducing phlegm, loosing silt, tonifying speen and tonifying kidney, relaxing muscles and tendons and activating QI and blood in the collateral.Early on the books in the Compendium of Material Medica of Ming Dynasty Li Shizhen (1518-1593 A.D.) work: Flos Osmanthi Fragrantis can " control all kinds of diseases and ailments, support spirit, and color, for all medicines are engaged logical making earlier, for a long time clothes make light of one's life by commiting suicide not old, the brilliance of looking unfamiliar, fawn on good normal as the boy "." origin of Chinese character " says that it is " fathers of hundred medicines " when explaining " osmanthus " word.Motherland's medical science is thought, Flos Osmanthi Fragrantis acrid in the mouth warm in nature has the effect of being good for the stomach, reducing phlegm, promoting the production of body fluid, loosing expectorant, suppressing the hyperactive liver.Modern medicine studies have shown that: Flos Osmanthi Fragrantis contains a large amount of flavone, oleanolic acid, ursolic acid, these materials all have antioxidation, anti-damaging action, hepatoprotective active substance of the present invention is a kind of of bisepoxy lignans's material, is soluble in organic solvent and alkaline aqueous solutions such as ethanol, acetone, chloroform.Up to now, the research and utilization of Flos Osmanthi Fragrantis is focused mostly in its volatile aromatic component, do not see the report that from Flos Osmanthi Fragrantis, extracts this active substance and carry out pharmacological research as yet.Based on above reason, the present invention studies in great detail the preparation technology of active substance in the Flos Osmanthi Fragrantis.
The method for extraction and purification of this active substance of having reported is: directly use organic solvent extraction, extract concentrates after column chromatography technology obtains product.The method that adopts when extracting active substance as Korea scholar Hyun Lim from Fructus Forsythiae is, at first use methanol extraction three times, after concentrating, extracting solution extracts with ethyl acetate and butanols respectively, the ethyl acetate part is through twice silica gel column chromatography, difference n-hexane/acetone and dichloromethane/acetone drip washing in varing proportions in front and back separates obtaining active substance.This method has been used a large amount of toxicity organic reagents, and parting material should not regenerate, and causes the production cost height.
Summary of the invention
The object of the present invention is to provide a kind of Flos Osmanthi Fragrantis extract, make it have the effect of hepatoprotective.Simultaneously, the present invention also provides the preparation method of this Flos Osmanthi Fragrantis extract.Further, the present invention also aims to provide the application of this Flos Osmanthi Fragrantis extract aspect hepatoprotective.
Below be to realize technical scheme of the present invention.
Flos Osmanthi Fragrantis extract with hepatoprotective effect provided by the invention is to be raw material with the Flos Osmanthi Fragrantis, according to the following steps Zhi Bei extract:
Step 1: Flos Osmanthi Fragrantis adding 3-8 doubly measures (w/v) solvent and fully extracts, and repeats to extract 2-3 time, and the extracting solution concentrating under reduced pressure gets extractum; Said solvent is methanol, ethanol, ethyl acetate or acetone; Said extracting method can for coldly ooze, warm macerating, supersound extraction, sudden strain of a muscle formula extract or reflux, extract; The used Flos Osmanthi Fragrantis raw material of the present invention can be flower, dry flower or the colored slag after Petroleum ether extraction is crossed spice, therefore the Flos Osmanthi Fragrantis resource is fully used;
Step 2: gained extractum mixes with adsorbent resin after doubly measuring (w/v) acetone solution with 2-3, and the back concentrating under reduced pressure that stirs reclaims solvent, the dry adsorption sample resin of gained upper prop; The weight in wet base of used adsorbent resin is 3-5 a times of extractum amount; Said adsorbent resin is nonpolar AB-8 or D101 macroporous adsorbent resin;
Step 3: with distilled water dash to eluate be colourless after, use solvent gradient elution instead, each gradient elution volume is a 4-6 times of column volume, the eluent flow is 0.5-1 times of column volume/h; Said gradient elution solvent is the methanol or the alcoholic solution of concentration 50%, 70% and 90%;
Step 4: concentrating under reduced pressure 70% methanol-eluted fractions solution or 90% ethanol elution solution promptly get flaxen Flos Osmanthi Fragrantis extract of the present invention after the pure recrystallizing methanol.
Flos Osmanthi Fragrantis extract warp of the present invention
1H-NMR with
13C-NMR is accredited as phillygenol, is hepatoprotective effective ingredient of the present invention.
The structure materials of identification of Flos Osmanthi Fragrantis extract of the present invention:
Flos Osmanthi Fragrantis extract of the present invention: pale yellow powder,
1H-NMR (400MHz, CDCl
3) and
13C-NMR (100MHz, CDCl
3) data (instrument is the AV400 of Switzerland Bruker company) are consistent with bibliographical information, determine that this chemical compound is phillygenol (Phillygenin).Bibliographical information phillygenol nuclear magnetic data is as follows:
1H-NMR (400MHz, CDCl
3) δ: 6.92-6.81 (6H, m, H-2,5,6,2 ', 5 ', 6 '), 4.87 (1H, d, J=5.5, H-7 '), 4.42 (1H, d, J=7.14, H-7), 3.87 (6H, s, 2 * OMe), 3.89 (3H, s, OMe), 4.12 (each 1H, m, H-9), 3.86,3.32 (each 1H, m, H-10), 3.35 (1H, m, H-8 '), 2.9 (1H, m, H-8);
13C-NMR (100MHz, CDCl
3) δ: 132.9 (C-1), 130.9 (C-1 '), 108.9 (C-2), 108.5 (C-2 '), 148.0 (C-3), 148.4 (C-3 '), 145.4 (C-4), 147.9 (C-4 '), 114.3 (C-5), 111.0 (C-5 '), 119.2 (C-6), 117.7 (C-6 '), 87.7 (C-7), 82.0 (C-7 '), 54.5 (C-8), 50.1 (C-8 '), 70.9 (C-9), 69.7 (C-9 ') (Wenyi Kang, Jinmei Wang.In vitroantioxidant properties and in vivo lowering blood lipid of Forsythiasuspense leaves, MEDICINAL CHEMISTRY RESEARCH, 05 June, 2009).The nuclear magnetic data of the active active substance of hepatoprotective is as follows in the Flos Osmanthi Fragrantis of being produced:
1H-NMR (400MHz, CDCl
3) δ: 6.90-6.83 (6H, m, H-2,5,6,2 ', 5 ', 6 '), 4.87 (1H, d, J=5.5, H-7 '), 4.42 (1H, d, J=7.14, H-7), 3.90 (6H, s, 2 * OMe), 3.87 (3H, s, OMe), 4.12 (each 1H, m, H-9), 3.86,3.32 (each 1H, m, H-10), 3.35 (1H, m, H-8 '), 2.9 (1H, m, H-8);
13C-NMR (100MHz, CDCl
3) δ: 133.0 (C-1), 131.0 (C-1 '), 109.0 (C-2), 108.6 (C-2 '), 148.0 (C-3), 148.8 (C-3 '), 145.4 (C-4), 146.7 (C-4 '), 114.3 (C-5), 111.1 (C-5 '), 119.2 (C-6), 117.8 (C-6 '), 87.7 (C-7), 82.0 (C-7 '), 54.5 (C-8), 50.1 (C-8 '), 71.1 (C-9), 69.7 (C-9 ').Fig. 1 and Fig. 2 are the active substance produced
1H-NMR with
13C-NMR collection of illustrative plates: Fig. 1 is
1The H-NMR collection of illustrative plates; Fig. 2 is
13The C-NMR collection of illustrative plates.Fig. 3 is that the HPLC of the Flos Osmanthi Fragrantis extract hepatoprotective active substance of example 1 preparation detects collection of illustrative plates.
The active animal data of Flos Osmanthi Fragrantis extract hepatoprotective of the present invention:
1, presses embodiment 1 preparation Flos Osmanthi Fragrantis extract of the present invention.
2, zoopery:
Method: by acute liver damage model and the indexs such as ALT, AST, SOD, MDA and tissue slice that carbon tetrachloride causes, the hepatoprotective activity of checking Flos Osmanthi Fragrantis extract of the present invention.Concrete experimental program is as follows:
The bifendate medication preparation: place mortar to grind drop pill, add the 0.5% carboxymethylcellulose sodium solution dissolving of certain volume, be made into 15mg/ml solution, standby.
Prepared by reagent liquid: Flos Osmanthi Fragrantis extract of the present invention (phillygenol) sample for preparing is configured to the medicinal liquid that concentration is 20mg/ml, 80mg/ml respectively with 0.5% carboxymethylcellulose sodium solution hydrotropy, and is standby.
50 of SPF level Kunming mouses, male and female half and half, body weight 20-25g is divided into 5 groups at random, every group 10, be respectively normal control group, model group, bifendate group (150mg/kg), phillygenol low dose group (200mg/kg), phillygenol high dose group (800mg/kg).Normal group and model group are irritated the stomach normal saline respectively, and all the other medicine groups are all irritated the stomach relative medicine, irritate stomach dosage and are 10ml/kg, continuous 10 days.Behind the 10th day perfusion 4h, the normal group intraperitoneal injection of saline, all the other respectively organize lumbar injection 0.1% carbon tetrachloride olive oil solution, cause the acute liver damage model, and injected dose is 0.1ml/kg.
Mice fasting after the hepatic injury is freely drunk water.Behind the 17h, mice is plucked eyeball and gets blood, the 6000r/min frozen centrifugation, and separation of serum is measured serum alt, AST content with reitman-frankel method.After mice was got blood, cervical vertebra dislocation was put to death, and it is fixing that the identical leaf of getting liver is put into formalin, paraffin embedding, and tissue pathological slice is done in HE dyeing; Another leaf liver is made liver homogenate after washing with cold saline in the ice bath, the 3000r/min frozen centrifugation is got supernatant, measures the content of SOD, MDA in the liver homogenate.
Result: ALT, AST physical signs experimental result are as shown in table 1: model group is compared with normal group, and serum alt, AST content obviously raise, and has the significance difference opposite sex (P＜0.001), and the model copy success of carbon tetrachloride acute liver damage is described.Compare with model group, phillygenol is low, high dose group all obviously reduces ALT, AST index, and is dose dependent, shows that Flos Osmanthi Fragrantis extract of the present invention (phillygenol) can alleviate hepatocyte injury.
Table 1. Flos Osmanthi Fragrantis extract of the present invention is to CCL
4Cause acute liver damage mice serum transaminase's influence
Compare with normal group: △ △ △ P＜0.001; Compare with model group: * P＜0.05, * * P＜0.01,
SOD, MDA physical signs experimental result are as shown in table 2: model group is compared with normal group, the SOD level reduces in the liver tissue homogenate, the MDA level obviously raises, and has the significance difference opposite sex (P＜0.05), illustrates that carbon tetrachloride causes the model copy success of acute liver damage.Compare with model group, phillygenol is low, high dose group all obviously reduces MDA content, the rising SOD activities of liver, and become dose dependent, show that phillygenol can effectively alleviate hepatocyte injury.
Table 2 Flos Osmanthi Fragrantis active substance is to CCL
4Cause the influence of acute liver damage mouse liver even slurry SOD and MDA
Compare with normal group: △ P＜0.05; Compare with model group: * P＜0.05
The tissue slice result: om observation is respectively organized the mice pathological section, finds that normal group mouse liver organizational structure is normal, can be observed tangible lobules of liver structure, and cell is arranged in order, and no balloon sample becomes, no spotty necrosis and focal necrosis.The model group mouse liver cell can obviously be observed balloon sample change and downright bad at microscopically, and the lobules of liver structural fuzzy is unclear in the visual field, and there is diffuse inflammatory cell infiltration central vein and portal area.Mouse liver cell balloon sample becomes and downright bad phenomenon all has alleviating in various degree in the Flos Osmanthi Fragrantis active substance treatment group, and wherein high dose group can be seen comparatively significantly lobules of liver structure, and cellularity is complete, seldom has the balloon sample to become and downright bad.Illustrate that Flos Osmanthi Fragrantis extract of the present invention has the hepatic injury of alleviating, liver-protective effect.
Above experimentation shows that Flos Osmanthi Fragrantis extract of the present invention (phillygenol) can effectively alleviate hepatocyte injury, has the hepatic injury of alleviating, liver-protective effect.Flos Osmanthi Fragrantis extract of the present invention (phillygenol) can be used for preparing to protect the liver protecting medicine.
The present invention has the following advantages:
1. the solvent toxicity that preparation method of the present invention is used is low, recyclable, environmental friendliness;
2. the used parting material physicochemical property of the present invention is stablized, and simultaneously organic compound is had good selectivity, is easy to regeneration and reuses;
3. the method flow of preparation Flos Osmanthi Fragrantis extract provided by the invention is simple, be convenient to operation, and extracted amount is big, scalable production;
4. adopt the present invention to obtain active substance purity greater than 90%, the separation efficiency height;
5. the present invention is raw materials used can be flower, dry flower or the colored slag after Petroleum ether extraction is crossed spice, therefore the Flos Osmanthi Fragrantis resource is fully used.
Description of drawings
Fig. 1 is for active substance that the present invention produced
1The H-NMR collection of illustrative plates;
Fig. 2 is for active substance that the present invention produced
13The C-NMR collection of illustrative plates;
Fig. 3 detects collection of illustrative plates (instrument is AgilentTechnologies 1200 Series) for the HPLC of Flos Osmanthi Fragrantis hepatoprotective active substance in the example 1.
The specific embodiment
Following case study on implementation is to describe in further detail of the present invention, but it does not mean that any limitation of the invention.
Example 1:
Get fresh Flos Osmanthi Fragrantis and add 95% ethanol with solid-to-liquid ratio 1: 5 (w/v), the back supersound extraction that stirs 2 times, each 20min filters, merging filtrate, concentrating under reduced pressure reclaims ethanol and gets extractum.Extractum mixes with the AB-8 macroporous resin of 3 times of amounts of weight in wet base after measuring acetone solutions with 2 times, and the back that stirs concentrates reclaims solvent, goes up macroporous resin column after the drying.With distilled water flushing to eluate is colourless, use gradient ethanol water flushing resin column instead, each gradient elution volume is 4 times of column volumes, flow is 0.75 times of column volume/h, concentrating under reduced pressure 90% ethanol elution, get faint yellow crystallization after the recrystallizing methanol, be the described Flos Osmanthi Fragrantis hepatoprotective of patent active substance, it is 94.81% that HPLC detects its content.
Example 2
Getting dried sweet-scented osmanthus is the acetone of 80% (v/v) with solid-to-liquid ratio (w/v) adding in 1: 8 content, and the sudden strain of a muscle formula is extracted 2 times, and each 5min filters, merging filtrate, and concentrating under reduced pressure reclaims acetone and gets extractum.Extractum mixes with the D101 macroporous resin of 5 times of amounts of weight in wet base after measuring acetone solutions with 3 times, and the back that stirs concentrates reclaims solvent, dry adsorption sample macroporous resin upper prop.It is colourless that water washes to eluate, use gradient ethanol water flushing resin column instead, each gradient elution volume is 5 times of column volumes, flow is 0.5 times of column volume/h, concentrating under reduced pressure 90% ethanol elution, get faint yellow crystallization after the recrystallizing methanol, be the described Flos Osmanthi Fragrantis hepatoprotective of patent active substance, it is 93.69% that HPLC detects its content.
Example 3
Get the colored slag that extracted behind the osmanthus spice and add 65% methanol with solid-to-liquid ratio 1: 5 (w/v), reflux, extract, 2 times, each 2h filters, and merging filtrate concentrates and reclaims methanol and get extractum.Extractum mixes with the AB-8 macroporous resin of 3 times of amounts of weight in wet base with 2 times of amount acetone solutions, and the back that stirs concentrates reclaims solvent, dry macroporous resin upper prop.It is colourless that water washes to eluate, use gradient ethanol water flushing resin column instead, each gradient elution volume is 4 times of column volumes, flow is 1 times of column volume/h, concentrating under reduced pressure 90% alcoholic solution, get faint yellow active substance product after the recrystallizing methanol, be the described Flos Osmanthi Fragrantis hepatoprotective of patent active substance, it is 92.11% that HPLC detects its content.
Example 4
Get dry Flos Osmanthi Fragrantis and add 90% ethanol with solid-to-liquid ratio 1: 4 (w/v), the back 50 ℃ of warm macerating that stir extract 2 times, and each 4-8h filters, merging filtrate, and the concentrated solvent that reclaims gets extractum.Extractum with 3 times of amounts (w/v) acetone solution after, mix with the AB-8 macroporous resin of 4 times of amounts of weight in wet base, solvent, dry macroporous resin upper prop concentrate to be reclaimed in the back that stirs.It is colourless that water washes to eluate, use gradient methanol aqueous solution flushing resin column instead, each gradient elution volume is 4.5 times of column volumes, flow is 1 times of column volume/h, concentrating under reduced pressure 70% meoh eluate, get faint yellow active substance product after the pure recrystallizing methanol, be the described Flos Osmanthi Fragrantis hepatoprotective of patent active substance, it is 92.05% that HPLC detects its content.
Example 5
Get fresh Flos Osmanthi Fragrantis and add ethyl acetate with solid-to-liquid ratio 1: 5 (w/v), cold oozing extracted 2 times after stirring, and each 3-5 days, filter, merging filtrate concentrates the recovery solvent and gets extractum.Extractum with 2 times of amounts (w/v) acetone solution after, mix with the D101 macroporous resin of 3 times of amounts of weight in wet base, solvent, dry macroporous resin upper prop concentrate to be reclaimed in the back that stirs.Water wash to eluate be colourless after, use gradient ethanol water flushing resin column instead, each gradient elution volume is 3 times of column volumes, flow is 1.5 times of column volume/h, concentrating under reduced pressure 90% ethanol elution, get faint yellow active substance product after the pure recrystallizing methanol, be the described Flos Osmanthi Fragrantis hepatoprotective of patent active substance, it is 90.37% that HPLC detects its content.
Claims (6)
1. Flos Osmanthi Fragrantis extract is characterized in that it is is raw material with the Flos Osmanthi Fragrantis, the material for preparing according to the following steps:
Step 1: Flos Osmanthi Fragrantis adding 3-8 doubly measures (w/v) solvent and fully extracts, and repeats to extract 2-3 time, and the extracting solution concentrating under reduced pressure gets extractum; Said solvent is methanol, ethanol, ethyl acetate or acetone; Said extracting method can for coldly ooze, warm macerating, supersound extraction, sudden strain of a muscle formula extract or reflux, extract;
Step 2: gained extractum mixes with adsorbent resin after doubly measuring (w/v) acetone solution with 2-3, and the back concentrating under reduced pressure that stirs reclaims solvent, the dry adsorption sample resin of gained upper prop; The weight in wet base of used adsorbent resin is 3-5 a times of extractum amount; Said adsorbent resin is nonpolar AB-8 or D101 macroporous adsorbent resin;
Step 3: with distilled water dash to eluate be colourless after, use solvent gradient elution instead, each gradient elution volume is a 4-6 times of column volume, the eluent flow is 0.5-1 times of column volume/h; Said gradient elution solvent is the methanol or the alcoholic solution of concentration 50%, 70% and 90%;
Step 4: concentrating under reduced pressure 70% methanol-eluted fractions solution or 90% ethanol elution solution promptly get flaxen Flos Osmanthi Fragrantis extract of the present invention after the pure recrystallizing methanol.
2. Flos Osmanthi Fragrantis extract according to claim 1 is characterized in that, described Flos Osmanthi Fragrantis can be flower, dry flower or the colored slag after Petroleum ether extraction is crossed spice.
3. the preparation method of a Flos Osmanthi Fragrantis extract may further comprise the steps:
Step 1: Flos Osmanthi Fragrantis adding 3-8 doubly measures (w/v) solvent and fully extracts, and repeats to extract 2-3 time, and the extracting solution concentrating under reduced pressure gets extractum; Said solvent is methanol, ethanol, ethyl acetate or acetone; Said extracting method can for coldly ooze, warm macerating, supersound extraction, sudden strain of a muscle formula extract or reflux, extract;
Step 2: gained extractum mixes with adsorbent resin after doubly measuring (w/v) acetone solution with 2-3, and the back concentrating under reduced pressure that stirs reclaims solvent, the dry adsorption sample resin of gained upper prop; The weight in wet base of used adsorbent resin is 3-5 a times of extractum amount; Said adsorbent resin is nonpolar AB-8 or D101 macroporous adsorbent resin;
Step 3: with distilled water dash to eluate be colourless after, use solvent gradient elution instead, each gradient elution volume is a 4-6 times of column volume, the eluent flow is 0.5-1 times of column volume/h; Said gradient elution solvent is the methanol or the alcoholic solution of concentration 50%, 70% and 90%;
Step 4: concentrating under reduced pressure 70% methanol-eluted fractions solution or 90% ethanol elution solution promptly get flaxen Flos Osmanthi Fragrantis extract of the present invention after the pure recrystallizing methanol.
4. the preparation method of Flos Osmanthi Fragrantis extract according to claim 3 is characterized in that, described Flos Osmanthi Fragrantis can be flower, dry flower or the colored slag after Petroleum ether extraction is crossed spice.
5. claim 1 or the 2 described Flos Osmanthi Fragrantis extracts application in preparation hepatoprotective medicine.
6. a medicine that is used for hepatoprotective is characterized in that containing claim 1 or 2 described Flos Osmanthi Fragrantis extracts as effective ingredient.
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| CN103223018A (en) * | 2013-05-08 | 2013-07-31 | 浙江大学 | Osmanthus fragrans polyphenol extract product, and preparation method and uses thereof |
| KR20150075757A (en) * | 2013-12-26 | 2015-07-06 | 동의대학교 산학협력단 | A composition comprising Osmanthus matsumuranus extracts having anti-cancer activity |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103223018A (en) * | 2013-05-08 | 2013-07-31 | 浙江大学 | Osmanthus fragrans polyphenol extract product, and preparation method and uses thereof |
| KR20150075757A (en) * | 2013-12-26 | 2015-07-06 | 동의대학교 산학협력단 | A composition comprising Osmanthus matsumuranus extracts having anti-cancer activity |
| KR101595987B1 (en) | 2013-12-26 | 2016-02-19 | 동의대학교 산학협력단 | A composition comprising Osmanthus matsumuranus extracts having anti-cancer activity |
| CN105078956A (en) * | 2014-05-19 | 2015-11-25 | 鲁南制药集团股份有限公司 | Application of forsythin aglycone in preparing medicine for preventing or treating liver injury or liver failure |
| CN107456411A (en) * | 2016-06-02 | 2017-12-12 | 上海家化联合股份有限公司 | A kind of skin epidermal cells vitality improver and its application in skin preparations for extenal use |
| CN107162805A (en) * | 2017-07-13 | 2017-09-15 | 烟台固特丽生物科技股份有限公司 | A kind of method that fresh flower extract prepares tea leaf quality modifying agent |
| CN113075016A (en) * | 2021-04-01 | 2021-07-06 | 上海应用技术大学 | Extraction process and activity determination method for ultrasonically-assisted flash extraction of osmanthus hydrolat |
| CN115715750A (en) * | 2021-09-30 | 2023-02-28 | 太和康美(北京)中医研究院有限公司 | Osmanthus fragrans flower extract, preparation method and skin care application thereof |
| CN115715750B (en) * | 2021-09-30 | 2023-08-04 | 太和康美(北京)中医研究院有限公司 | Osmanthus fragrans extract, preparation method and skin care application thereof |
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Application publication date: 20110608 |